Cyclic process of making aromatic hydrocarbon hydroxy compounds.



cultly soluble calcium sulfate by treatment LOUIS M. name, or rrnaca, nnw roan.-

GYCLIC PROCESS OF MAKING- .A ROMATIC HYDROGARBQN DROXY COMPOUNDS.

iueaaseag no Drawing.

of New York, haveinvented certain new and useful Improvements in Cyclic Processes of Making Aromatic Hydrocarbon Hydroxy Compounds, .of which the followmg is a specification.

1Q My invention relates to a cyclic process making aromatic hydrocarbon hydroxy compounds wherein I am enabled 'to omit certam hitherto usual steps of operation with consequent simplifying of the process.

I shall illustratemy invention by describing a process of making phenol from an aromatic hydrocarbon sulfonic acid, whereamong other things, I am enabled, for

to omit the usual steps-of removexample,

sulfuric acid in the form 'of difiing the with lime and sodium compounds.

In the practice of my process. and to form the aromatic hydrocarbon sulfonic acid to be thereafter reacted upon, in this illustration benzene sulfonic acid, I may proceed as follows: I treat benzene with sulfuric acid, preferably fuming sulfuricacid, to

produce benzene' sulfonic acid in excess of sulfuric acid. ..I treat this mixture with benzene and, as the sulfuric acid is practically insoluble in benzene, the benzene '5 benzene sulfonic acid substantially free from 5' takes up the benzene sulfonic acid, but not sulfuric I acid to any appreciable extent,

forming a benzene-solution of benzene sul- ,fonic acid' substantially free from'sulfuric treat this benzene solution of ben-- acid. I zene sulfonic acid withiwater Which dissolves out the benzene sulfonic acid and sep- -arates the same from the benzene;

In order to initiate the process and to produce the initial charge of sodium benzene sulfonate, I may then treat the aqueous solution of benzene sulfonic acid substantially free from sulfuricacid with an aqueous solution of sodium hydroxid or other suitable sodium compound or mixture of such compounds, to form -SOdllllIl benzene sulfonate. This is separated from the solution, dried, and fused with solid sodium hydroxid forming sodium phenolate together with sodium sulfite. The sodium phenolate is then treated with an aqueous solution of and sodium sulfuric acid forming phen'ol v be separated benzene sulfonate, WhlCh may Specification ofLetters Pateiit.

by suitable means. The solution of sodium benzene sulfonate is then evaporated to dryness and the dry sodium benzene ,sulfonate then fused with solid sodium hydroxid Patented May 29, mm. Application filed July 14, 1916. "Serial no. 109,212.

forming as before sodium phenolate and sodium sulfite. The sodium phenolate is then neutralized with a fresh charge of benzenesulfonic acid substantially free from sulfuric acid formin as before, phenol and sodium benzene sul onate and the process repeated. The sodium sulfite which isformed in the process is removed from time to time as may be necessary.

The reactions may be illustrated substantially as follows G H SO Na+2NaOH (fused):

I G H' 0Na-{ Na SO -I-H G H ONa+G H SO H= 'fi fi OH-l-fl fi sO Na C,H,SO Na-|-2NaOl-l (fused):

G H ONa+Na SO +H O andso'on. v

It will be noted that the sodium benzene sulfonate which is one of the products of reaction on the neutralization of sodium phenolate by benzene sulfonic acid, is again used to be fused with solid sodium hydroxid' to again produce sodium phenolate which is inturn neutralized by fresh benzene sulfonic acid substantially free from sulfuric acid, producing phenol and sodium benzene sulfonate again in a cyclic process. 7

"It isobvious that the process is not restricted to the making of phenol as other aromatic hydrocarbon hydroxy bodies may be formed in a similar manner. Where I speak of sulfuric acid being insoluble in benzene I mean of course that it is practically so and where, in the claims, I refer to sulmean that sulfuric acid is not present in .the benzene sulfonic acid to any appreciable extent. Furthermorefin order to initially sulfonic acid with an oxy alkali salt of said Y furic-acid-free benzene, sulfonic acid, T

hydrocarbon sulfonic acid, separating the products of the reaction, fusing the alkali salt with an alkali hydroxid to again produce the oxy alkali salt of the aromatic hydrocarbon, and treating the latter With a fresh charge of sulfuric-acid-free aromatic hydrocarbon sulfonic acid, and repeating the steps.

2. 'A cyclic process of making phenol consisting in reacting on an aqueous solution of sulfuric-acid-free benzene sulfonic acid with an alkali phenolate to form phenol and the alkali benzene sulfonate, separating the products of the reaction, fusing the sulfonate With alkali hydroxid to again produce alkali phenolate, and treating the latter 1,227,,sea-

with a fresh charge of sulfuric-acid-free benzene sulfonic acid, and repeating the steps.

3. A cyclic process of making phenol consisting in reacting on an aqueous solution of sulfuric-acid-free benzene sulfonic acid With sodium phenolate to form phenol and sodium benzene sulfonate, separating the products of the reaction, fusing the sulfonate with sodium hydroxid to again produce sodium phenolate, and treating the latter with a fresh charge of sulfuric-acidfr'ee benzene sulfonic acid, and repeating the steps.

In testimony whereof- I have signed this specification. I

Louis M. DnNNis. 

